The beginning of writer-director Jay Duplass’ Christmas Eve rom-com The Baltimorons is alarmingly dark, opening with a non-fatal suicide attempt by its male protagonist. That doesn’t exactly set the scene for 100 minutes of holiday cheer, but The Baltimorons is ultimately a hopeful tale packed with charming quirks, lulling quietude, vivid characterization and an unlikely May-December romance.
With so much talk about age-gap relationship films — usually in the derogatory sense, sometimes in the spicy, controversially thrilling sense — The Baltimorons may feel trendy, if not a byproduct of previous trends. In 2024 and 2025, Lonely Planet, Queer, Babygirl, The Idea of You, A Family Affair and Bridget Jones: Mad About the Boy all featured significant age-gap relationships. Of those six films, five of them center on romances between older women and younger men (and two of them star Nicole Kidman, but that’s peripheral). The Baltimorons, however, is in its own league.
Duplass refuses to sensationalize the age-gap flirtation between Didi (Liz Larsen), a mildly curmudgeonly and very stern divorceé “MILF dentist,” and Cliff (Michael Strassner), a newly sober former improv comedian begrudgingly looking to become a mortgage broker. Their individual places in life are relevant, if not strategic; still, age is but a number. Didi and Cliff are just two lost and lonely souls who connect on a strange Christmas Eve in Baltimore, wandering the city and committing felonies in the gentlest of ways.
The soft, dialogue-driven touch of indie filmmaker Duplass — who is often associated with the early ’00s mumblecore film movement alongside his brother Mark — and the tantalizing comedy chops of co-writer and star Michael Strassner make The Baltimorons the refreshing Christmas gift that keeps on giving. (Jay Duplass told MovieWeb in a 2025 interview that mumblecore came from necessity, saying, “we were just trying to make a movie that was affordable and didn’t suck.”)
An unlikely duo, each facing respective familial and love life tensions, is brought together during the holidays by way of a cracked tooth? That’s a recipe for a heartfelt series of misadventures, all of which feel surprisingly rooted in reality. (This isn’t a guilty pleasure Hallmark cheese fest.) A night of sardonic humor, primal attraction and reflecting on the past help Didi and Cliff live life once again, surrounded by the glow of Christmas lights, the salty scent of fresh crabs and the taste of Cliff’s sweet potatoes with candied pecans.
An Improbable Dentist’s Office Meet-Cute
Cliff cracks his molar when he slips on a loose brick nestled in the front steps of his fiancée Brittany’s (a wonderfully emotive Olivia Luccardi) parents’ house. This was after the couple celebrated Cliff’s six-month AA chip, which quickly turned into a dispute about Cliff’s friend Marvin (Rob Phoenix) inviting him to a comedy show on Christmas Eve. Initially, Brittany’s behavior comes across as nagging, but it’s soon revealed that the comedy scene is where much of Cliff’s drinking happened. Brittany was around for Cliff’s darkest moments, and with his location ever-present on her phone, her panicky, almost maternal characteristics are a direct result of Cliff’s past. The couple’s masterfully executed quarrel suggests that both partners are permanently altered, establishing their shaky relationship dynamic less than five minutes into the film. Soon, it also becomes clear Cliff doesn’t want the traditional white picket fence life that Brittany desperately desires.
Enter Didi, the only dentist in Baltimore who’s enough of a workaholic to take a patient on a holiday. Thinking that she’s hosting a dinner for her daughter and granddaughter later that evening, Didi assumes one quick emergency patient can’t hurt. After Cliff stumbles into her office with a bloody kitchen towel stuffed in his mouth, however, she receives a phone call from her daughter Shelby (Jessie Cohen).
As it turns out, Didi’s nightmare ex-husband, Conway (Brian Mendes), married his much younger fiancée, Patty (a hilarious Mary Catherine Garrison, who Duplass previously directed in HBO’s Somebody Somewhere), at the courthouse that morning. He’s also throwing a spontaneous reception of sorts later that day, and Shelby feels pressured to attend. Suddenly, Didi’s Christmas Eve dinner is canceled, and she is crushed.
Didi ignores Cliff’s flirtatious comments, pulled from the privacy of his thoughts by laughing gas, as she does her magic. Then Cliff discovers that his car was towed. Watching Cliff have a pathetic phone conversation with an irritated Brittany, Didi’s empathy kicks in. Didi offers to drive Cliff to the tow yard, beginning an audacious night of tomfoolery, non-violent crime, party-crashing, improvisation — both on stage and in life — and unforeseen revelations. With so many incidents and mishaps leading up to their equally intimate and whimsical night, The Baltimorons can be seen as a tale of fate, or perhaps beautifully coincidental timing. Either way, Cliff and Didi’s connection is real.
Without Jay Duplass discovering Michael Strassner’s Instagram — essentially a portfolio of goofy sketches featuring impersonations of everyone from Truman Capote to Buffalo Bill — The Baltimorons would never have happened. And without Duplass, a Transparent series alum, seeing Liz Larsen shine in A Transparent Musical, the film’s stirring chemistry wouldn’t have been the same. These events are as organic as the romance that unfolds in The Baltimorons.
And while Strassner cheekily relayed to MovieWeb that he’s never dated a dentist, the character of Cliff is based on Strassner’s own life. The distressing opening scene, featuring a chair, an attic, a snapped noose belt and “a bit of holiday weight,” is the real reason Strassner got sober. He really is a Baltimore native and an improv comedian who thought he’d no longer be a hoot without alcohol. And as is shown in the film, booze is never what made Cliff — or the man who plays him — genuinely funny.
Some of The Baltimorons‘ funniest gags are dark ones: When Cliff tells Didi that he attempted to end his own life six months prior, mentioning the holiday weight and the broken belt, she asks, “What holiday was six months ago?” He replies, “I had, like, 40 corn dogs on the Fourth of July, but that was after the attempt.” This pitch-black comedy fares well alongside sweet and silly moments like Cliff’s joke about muralist Gaia’s vivid portrait of Mr. Ed the cat. A cozy Peanuts-esque score and Duplass’ mellow direction also lend the film a certain tranquility, with a clear nod to the delightful nature of the Charm City.
The Baltimorons works for many reasons. As far as performances go, Larsen’s measured approach to Didi’s eventual softening and emotional openness is stunning. Strassner is equally magnetic, bringing a believably lovable teddy-bear vibe to an otherwise messy character. This could’ve been another hackneyed, soulless, cavity-inducing (pun intended) holiday rom-com; instead, it’s a brilliant portrait of life’s most tender and eye-opening moments, the kind that play out when you least expect them to.
From IFC and Sapan Studios, The Baltimorons releases in New York theaters on September 5, 2025, with an expansion starting on September 12th.
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